s‑Tetrazine Dyes: A Facile Generation of Photoredox Organocatalysts for Routine Oxidations

A series of organic dyes derived from s-tetrazine have been synthesized, and their photophysical and electrochemical properties are systematically investigated. Testing these compounds as photoredox catalysts in a model oxidative C–S bond cleavage of thioethers has led us to identify new classes of...

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Veröffentlicht in:Journal of organic chemistry 2019-12, Vol.84 (24), p.16139-16146
Hauptverfasser: Le, Tuan, Courant, Thibaut, Merad, Jérémy, Allain, Clémence, Audebert, Pierre, Masson, Géraldine
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Sprache:eng
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Zusammenfassung:A series of organic dyes derived from s-tetrazine have been synthesized, and their photophysical and electrochemical properties are systematically investigated. Testing these compounds as photoredox catalysts in a model oxidative C–S bond cleavage of thioethers has led us to identify new classes of active s-tetrazines. Moreover, some of them can be formed in situ from commercially available 3,6-dichlorotetrazine, making this photocatalyzed C–S bond functionalization simple and highly practical.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02454